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A versatile access to new halogenated 7-azidocoumarins for photoaffinity labeling: Synthesis and photophysical properties
Authors:Emilia PǎunescuLudivine Louise  Ludovic Jean  Anthony Romieu  Pierre-Yves Renard
Affiliation:a Equipe de Chimie Bio-Organique, COBRA - CNRS UMR 6014 & FR 3038, rue Tesnière, 76130 Mont-Saint-Aignan, France
b Université de Rouen, Place Emile Blondel, 76821 Mont-Saint-Aignan, France
c Institut Universitaire de France, 103 Boulevard Saint-Michel, 75005 Paris, France
Abstract:A versatile methodology for the synthesis of 6/8-halogenated 7-aminocoumarins from the corresponding 7-hydroxy analogs using Pd-catalyzed amination reaction as the key step is presented. Further readily conversion into 7-azidocoumarins was performed and the resulting aryl azides proved higher stability and reactivity than the corresponding non-halogenated parent compound. These new compounds may thus constitute attractive scaffolds for designing novel photoaffinity reagents for various challenging bio-labeling applications.
Keywords:Aryl azides   Coumarins   Pd-catalyzed amination   Photoaffinity labeling   Photochemistry   Pro-fluorescence
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